Cheshire Community YMCA Harvest Trail Race and Y Cup Relay
- Date Sat 24th October 2026
- Time 9:45AM EDT
- Location Cheshire, Connecticut
- Price Free - $41.28
- Races 3 races
- Distances 5km
Event summary
Get ready for a fantastic day of fun and fitness at the Cheshire Community YMCA Harvest Trail Race and Y Cup Relay on Saturday, October 24, 2026! Set against the scenic backdrop of historic Ives Farm in Cheshire, Naugatuck Valley, this exciting event features a 5K run and the thrilling Y Cup Relay, perfect for runners of all ages and skill levels. The race kicks off with a FREE Pumpkin Dash for kids aged 6 and under at 9:45 AM, followed by the 5K at 10:00 AM and the Y Cup Relay at 10:05 AM.
Beyond the races, the day promises a delightful array of family-friendly activities, including pumpkin decorating, face painting, Halloween mask making, engaging games, live music, and a fall-themed photo booth. By participating in this vibrant community event, you'll not only enjoy a day of outdoor adventure but also support the vital work of the YMCA and the revitalization efforts of the Cheshire Land Trust for the Ives Farm property. Mark your calendars and join us for a memorable day of celebration and community spirit!
Beyond the races, the day promises a delightful array of family-friendly activities, including pumpkin decorating, face painting, Halloween mask making, engaging games, live music, and a fall-themed photo booth. By participating in this vibrant community event, you'll not only enjoy a day of outdoor adventure but also support the vital work of the YMCA and the revitalization efforts of the Cheshire Land Trust for the Ives Farm property. Mark your calendars and join us for a memorable day of celebration and community spirit!
Organiser's Description
The Cheshire Community YMCA and Cheshire Land Trust are partnering on a race around historic Ives Farm. This all-ages run will wind through the fields and trails on the property, with the start and finish line located at the beautifully restored barn. Proceeds from this event will support the work that the YMCA does in the Cheshire community as well as the revitalization plans that the Cheshire Land Trust has for the Ives Farm property.
* Prior to the race there will be a FREE Pumpkin Dash for kids 6 years old and younger.
* Family friendly activities include pumpkin decorating, face painting, Halloween mask making, games, live music and a fall theme photo booth
Pumpkin Dash Start: 9:45AM
5K Start: 10:00AM
Y Cup Relay Start: 10:05AM
* Prior to the race there will be a FREE Pumpkin Dash for kids 6 years old and younger.
* Family friendly activities include pumpkin decorating, face painting, Halloween mask making, games, live music and a fall theme photo booth
Pumpkin Dash Start: 9:45AM
5K Start: 10:00AM
Y Cup Relay Start: 10:05AM
Races
-
5K Trail Race
Incl. $3.28 Fee & Custom Harvest Trail Race Hat
Sat 24th October 2026 (10:00AM EDT)
$41.28
This trail 5k is a great beginner friendly race with varied terrain and some slight elevation - perfect for the road runner wanting to try a trail run. It's also a good opportunity for an experienced trail runner to do some speed work. -
Y Cup Relay
Incl. $2.02 Fee & Custom Harvest Trail Race Hat
Sat 24th October 2026 (10:05AM EDT)
$19.02
Teams of 3 elementary school students will each run one mile of the 5K course. Teams from all grades will compete for their team to determine which school wins the prestigious Y Cup for the 25-26 school year. This years Y Cup Relay will be run in honor of Coach Jerry Webb who was a beloved Physical Education teacher at Highland School and an active part of the Y Cup Relay since it began. His support and enthusiasm for this event was contagious and resulted in a great turn out of young runners. -
Pumpkin Dash
Incl. Finisher Medal
Sat 24th October 2026 (9:45AM EDT)
Free
A free race for kids 6 and under on the dirt roads of Ives Farm. Kids will get a chance to run through the same race finish line as all other racers.
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1585 Cheshire St., Cheshire, 06410, CT, United States
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Cheshire Community YMCA Harvest Trail Race and Y Cup Relay
